This invention relates to benzofuran and benzothiophene sulfonamides which are novel. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g., plant growth regulants and herbicides. The invention also includes intermediates useful for making these compounds.
Netherlands Patent No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein
R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein
R.sub.1 is hydrogen or lower saturated aliphatic acyl and
R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein
R.dbd.H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein
R is butyl, phenyl or ##STR5## and
R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6##
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula ##STR7## wherein ##STR8##
R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl;
R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;
R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;
R.sub.8 is hydrogen, methyl, chlorine or bromine;
R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine;
W and Q are independently oxygen or sulfur;
n is 0, 1 or 2;
X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and
Z is methyl or methoxy; or their agriculturally suitable salts; provided that:
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 (1) in Formulae II and II', when R.sub.5 is NO.sub.2, then R.sub.6 is C.sub.1 -C.sub.4 alkyl and R.sub.6 ' is CH.sub.3 ; PA1 (2) when X is Cl or F, then Z is CH and Y is OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (3) when Q is SO, then W is O; PA1 (4) when R.sub.4 is other than H, then R.sub.5 is H; and PA1 (5) R.sub.1 and R.sub.2 taken together are not more than four carbon atoms. PA1 (1) Compounds of the generic scope of Formula I. PA1 (2) Compounds of Preferred 1 where W is O. PA1 (3) Compounds of Preferred 2 where R.sub.5 is H, Cl, CH.sub.3, OCH.sub.3, CO.sub.2 R.sub.7 or SO.sub.2 R.sub.8, R.sub.4 is H, Cl, CH.sub.3 or OCH.sub.3, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2, ##STR13## C.sub.2 H.sub.5, CF.sub.3, CH.sub.2 .dbd.CHCH.sub.2 O, HC.tbd.CCH.sub.2 O, CF.sub.3 CH.sub.2 O, OCF.sub.2 H or SCF.sub.2 H. PA1 (4) Compounds of Preferred 3 where R.sub.3, R.sub.4, R.sub.5 and R.sub.12 are H, R.sub.1 is H, CH.sub.3 or CH.sub.2 CH.sub.3 and R.sub.2 is H or CH.sub.3. PA1 (5) Compounds of Preferred 4 where A is ##STR14## Z is CH or N; and X is CH.sub.3, OCH.sub.3 or Cl. (6) Compounds of Preferred 5 where Y is CH.sub.3, OCH.sub.3, CH.sub.2 OCH.sub.3 or N(CH.sub.3).sub.2. PA1 (7) Compounds of the generic scope of Formula I'. PA1 (8) Compounds of Preferred 7 where W is O and Q is S or O. PA1 (9) Compounds of Preferred 8 where R.sub.5 is H, Cl, CH.sub.3, OCH.sub.3, CO.sub.2 R.sub.7 or SO.sub.2 R.sub.8 ; and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2, ##STR15## C.sub.2 H.sub.5, CF.sub.3, CH.sub.2 .dbd.CHCH.sub.2 O, HC.tbd.CCH.sub.2 O, CF.sub.3 CH.sub.2 O, OCF.sub.2 H or SCF.sub.2 H. PA1 (10) Compounds of Preferred 9 where R.sub.5 and R.sub.12 are H and R.sub.1 and R.sub.2 are independently H or CH.sub.3. PA1 (11) Compounds of Preferred 10 where A is ##STR16## Z is CH or N; and X is CH.sub.3, OCH.sub.3 or Cl. (12) Compounds of Preferred 11 where Y is CH.sub.3, OCH.sub.3, CH.sub.2 OCH.sub.3 or N(CH.sub.3).sub.2. PA1 (13) Compounds of the generic scope of Formula II. PA1 (14) Compounds of Preferred 13 where W is O, R.sub.6 is H, CH.sub.3 or CH.sub.2 CH.sub.3 and R.sub.6 ' is H. PA1 (15) Compounds of Preferred 14 where R.sub.5 is H, Cl, CH.sub.3, OCH.sub.3, CO.sub.2 R.sub.7 or SO.sub.2 R.sub.8, R.sub.4 is H, Cl, CH.sub.3 or OCH.sub.3, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2, ##STR17## C.sub.2 H.sub.5, CF.sub.3, CH.sub.2 .dbd.CHCH.sub.2 O, HC.tbd.CCH.sub.2 O, CF.sub.3 CH.sub.2 O, OCF.sub.2 H or SCF.sub.2 H. PA1 (16) Compounds of Preferred 15 where R.sub.4, R.sub.5, R.sub.6 ' and R.sub.12 are H and R.sub.6 is H or CH.sub.3. PA1 (17) Compounds of Preferred 16 where A is ##STR18## Z is CH or N; and X is CH.sub.3, OCH.sub.3 or Cl. (18) Compounds of Preferred 17 where Y is CH.sub.3, OCH.sub.3, CH.sub.2 OCH.sub.3 or N(CH.sub.3).sub.2. PA1 (19) Compounds of the generic scope of Formula II'. PA1 (20) Compounds of Preferred 19 where W is O, Q is O or S, R.sub.6 is H or CH.sub.3 and R.sub.6 ' is H or CH.sub.3. PA1 (21) Compounds of Preferred 20 where R.sub.5 is H, Cl, CH.sub.3, OCH.sub.3, CO.sub.2 R.sub.7 or SO.sub.2 R.sub.8 ; and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2, ##STR19## C.sub.2 H.sub.5, CF.sub.3, CH.sub.2 .dbd.CHCH.sub.2 O, HC.tbd.CCH.sub.2 O, CF.sub.3 CH.sub.2 O, OCF.sub.2 H or SCF.sub.2 H. PA1 (22) Compounds of Preferred 21 where R.sub.5 and R.sub.12 are H. PA1 (23) Compounds of Preferred 22 where A is ##STR20## Z is CH or N; and X is CH.sub.3, OCH.sub.3 or Cl. (24) Compounds of Preferred 23 where Y is CH.sub.3, OCH.sub.3, CH.sub.2 OCH.sub.3 or N(CH.sub.3).sub.2.
In addition, U.S. Ser. No. 227,886 teaches o-alkylsulfonylbenzenesulfonylureas which are useful as herbicides.
In U.S. Ser. No. 274,233, there is a disclosure of herbicidal benzo[b]thiophene- and benzofuransulfonylureas in which the sulfonylureido group is bonded to the heterocyclic ring.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.